This invention provides methyl substituted 2-(2,6-dimethyl-1,5-heptadienyl)-1,3-dithiolanes defined according to the generic structure: ##STR2## wherein R.sub.1 and R.sub.2 are the same or different and each represents methyl or hydrogen with the proviso that at least one of R.sub.1 and R.sub.2 is methyl and uses thereof in augmenting or enhancing the aroma or taste of foodstuffs.
Artificial flavoring agents for foodstuffs have received increasing attention in recent years. In many areas, such food flavoring agents are preferred over natural flavoring agents at least in part because of the uniform flavor that may be so obtained. For example, natural food flavoring agents such as extracts, essences, concentrates and the like are often subject to wide variation due to changes in the quality, type and treatment of the raw materials. Such variation can be reflected in the end product and results in unreliable flavor characterists and uncertainty as to consumer acceptance and cost. Additionally, the presence of the natural product in the ultimate food may be undesirable because of increased tendency to spoil. This is particularly troublesome in convenience and snack food usage where such products as dips, soups, chips, prepared dinners, canned foods, sauces, gravies and the like are apt to be stored by the consumer for some time prior to use.
The fundamental problem in preparing artificial flavoring agents is that of achieving as nearly as possible a true flavor reproduction. This generally proves to be a difficult task since the mechanism for flavoring development in many foods is not understood. This is notable in products having cooked liver, liverwurst, and rare liver aromas and cooked liver, liverwurst, fatty and rare liver tastes with hydrolyzed vegetable protein-like aftertastes.
Reproduction of cooked liver, liverwurst and rare liver aromas and cooked liver, liverwurst, rare liver and fatty tastes with hydrolyzed vegetable protein aftertastes has been the subject of a long and continuous search by those engaged in the production of foodstuffs. The severe shortage of foods, especially protein foods, in many parts of the world has given rise to the need for utilizing non-meat sources of proteins and making such proteins as palatable and as meat-like as possible. Hence, materials which will closely simulate or exactly reproduce flavor and aroma of liverwurst are required. Furthermore, meat flavors have been enhanced previously by the use of such materials as monosodium glutamate. In many diets, sodium is not desired. In many other diets, monosodium glutamate is not desired. Therefore a need has arisen for a monosodium glutamate replacer.
Moreover, there are a great many meat containing or meat based foods presently distributed in a preserved form. Examples of such substances are condensed soups, dry soup mixes, dry meat, freeze dried or lyophilized meats, packaged gravies and the like. While these products contain meat or meat extracts, the fragrance, taste and other organoleptic factors are very often impaired by the processing operation and it is desirable to supplement or enhance the flavors of these preserved with versatile materials which have cooked liver, liverwurst, and/or rare liver aromas and cooked liver, liverwurst, and/or rare liver and/or fatty tastes with hydrolyzed vegetable protein aftertastes.
Furthermore, there is a need for pet foods (e.g. dog foods and cat foods) which have cooked liver, liverwurst, and rare liver aromas and cooked liver, liverwurst, rare liver and fatty tastes with hydrolyzed vegetable protein-like aftertastes. There are great many pet foods presently distributed in a preserved form. Examples of such are dry meat, freeze dried or lyophilized meats, packaged gravies and the like. While these products contain meat or meat extracts, they also contain additional proteinaceous materials and the fragrance, taste and other organoleptic factors are very often impaired by the processing operation and by the presence of selected proteinaceous materials. It is thus desirable to supplement or enhance the flavors of these pet foods which are preserved with versatile materials which have cooked liver, liverwurst, and rare liver aromas and cooked liver, liverwurst, fatty and rare liver tastes with hydrolyzed vegetable proteinlike aftertastes.
Alkanes having 3-methylthio moieties are known in the prior art, for example, that disclosed in Chem. Abstracts, Volume 96, No. 103327y having the structure: ##STR3## This abstract is of Tetrahedron Letters, Vol. 22, number 42, pages 4159-4162, 1981, (Title: "Thiosulfonium Ions. Methylthiolation of 3-methylthio-1-butene and cis- and trans-1-methylthio-2-butene": Kim and Caserio).
Chem. Abstracts, Vol. 96:20080m which is an abstract of Fischer, Liebigs Ann. Chem., 1981 (10), 1899-1902 discloses the compound having the structure: ##STR4## wherein n is 2, 3 or 4 but does not disclose its organoleptic utilities.
Chem. Abstracts, Vol. 84:164792v, (abstract of German Offenlegungsschrift 2,530,273) discloses the compound having the structure: ##STR5## but does not disclose its organoleptic utilities,
U.S. Pat. No. 4,153,442 issued on May 8, 1979; U.S. Pat. No. 4,224,051 issued on Sept. 23, 1980; and U.S. Pat. No. 4,101,307 issued on June 18, 1978 each discloses plant growth regulating materials compounds defined according to the generic structure: ##STR6## in which X and Y which may be the same or different and represent oxygen, sulphur or a radical N--B where B is hydrogen, a lower alkyl radical containing 1 to 4 carbon atoms, an optionally substituted aryl radical or an optionally substituted acyl radical containing from 1 to 4 carbon atoms;
R and R' which may be the same or different and represent a lower alkyl radical containing from 1 to 4 carbon atoms or an acyl or amido radical containing from 1 to 4 carbon atoms; in addition they may form with ##STR7## PA0 A represents either a single bond or an alkylene chain containing from 1 to 4 carbon atoms optionally interrupted by an oxygen atom or a group N--B' where B' represents hydrogen, an optionally halogenated or hydroxylated alkyl group, an acyl group, the hydrocarbon portion of these radicals containing from 1 to 4 carbon atoms, or a cycle having in common with the preceding cycle 1 to 2 carbon atoms and containing from 3 to 6 carbon atoms, from 0 to 2 oxygen atoms and/or a group N--B, or a cycle corresponding to the formula ##STR9##
a cycle corresponding to the formula ##STR8## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different and represent hydrogen, an alkyl radical containing from 1 to 4 carbon atoms and optionally substituted by a halogen, the radicals NO.sub.2, hydroxy or alkoxy containing from 1 to 4 carbon atoms;
Included in this generic structure is the genus defined according to the structure: ##STR10##
Nagao, et al, Tetrahedron Letters No. 34, pages 3167-3168 (1979) discloses the genus of compounds defined according to the structure: ##STR11## in a synthetic route to yield certain ketones. In this genus R may be methyl, ethyl, propyl, butyl, tolyl, tolyl methoxy, allyl or phenyl.
Nothing in the prior art discloses the methyl substituted 2-(2,6-dimethyl-1,5-heptadienyl)-1,3-dithiolanes of our invention or its organoleptic uses however.